I genuinely cannot believe I’m writing this, but Benny is starting his 2s program! Somehow my tiny baby is officially going to SCHOOL, and I am equal parts emotional and so excited for him.
Obviously, I used this major life milestone as an excuse to shop. But I really wanted to make sure we had everything ready to make our mornings as easy as possible. From the backpack and labels to the little sneakers and jackets I know he’ll live in all fall, I rounded up everything I bought for his first year of 2s.
Some of it is very necessary, some of it is very cute, and some of it is probably the result of me coping with the fact that my baby is old enough to have a backpack. Either way, here is the full Benny Goes to School edit!
The Cool Mom’s Guide to Starting 2s
The School Essentials
First things first: all the stuff he actually needs. I wanted everything Benny brings to school to be functional, toddler-proof, and obviously still cute.
I mean, is there anything cuter than a tiny personalized nap mat?! I love the little trucks, and having his name on everything is officially my new personality.
All the compartments make packing toddler lunches and snacks so much easier, and I love that everything stays separated.
Sturdy, easy to clean, and can survive being thrown around by a two-year-old. Enough said.
The perfect size for him and SO cute without feeling too baby-ish. Watching him wear his own little backpack might actually send me over the edge.
Apparently starting school means labeling literally EVERYTHING 😂 Clothes, water bottles, lunchboxes, nap mats—you name it, his name is going on it.
The 2s Uniform
For school clothes, I’m keeping it cute, comfortable and very easy. Things he can run around in, get messy in, and I won’t be devastated when they inevitably come home covered in paint, dirt and snacks.
I stocked up on the baby boy striped tees because they make even the easiest toddler outfit feel a little more put together. I love a stripe on a little boy.
Soft, comfy, inexpensive enough for school, and easy for him to actually play in. Basically exactly what I want for 2s.
Anything he can run around in all day and that doesn’t make getting out the door harder than it needs to be.
Fall Jackets + Layers
Washed Utility Jacket for Toddler Boys
You know I can’t resist a tiny jacket, so naturally his school outerwear needed its own edit too.
My formula for his first year of school is basically striped tee + comfy pants + sneakers + a cute jacket.
What’s in His Cubby
The other thing I quickly learned about starting 2s is that the cubby needs to be STOCKED. Basically, I’m preparing for every possible toddler scenario. Here’s what I’m keeping at school for Benny:
For the inevitable wet, muddy, paint-covered or otherwise questionable outfit that needs to come home.
A little raincoat + rain boots for those wet school mornings and outdoor play days.
For art projects and all the messiness that comes with 2s—if your school doesn’t already provide one.
A little fork + spoon set for lunches that require more than tiny hands.
For anything that doesn’t fit directly into the PlanetBox or for sending an extra snack.
If your school allows you to keep one there, I love having a designated bottle so I’m not constantly remembering to pack it.
Extra Change of Clothes
A full backup outfit: tee, comfy pants, socks, plus underwear or diapers depending on where you are with potty training. I’ll probably keep more than one set there because… toddlers.
Family Photo
Some 2s classrooms ask you to send in a family photo for their cubby or classroom, which may be the sweetest school supply of all. And yes, this one might make me cry.
Done. And now I just need to emotionally prepare myself for drop-off.
